Summerland Key vacation rentals

We found 747 vacation rentals — enter your dates for availability

Select from 479 homes, 54 cottages, and other vacation rentals in Summerland Key to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Summerland Key

Why visit Summerland Key

  1. Stunning Beaches: Enjoy beautiful beaches like Sunset Beach, perfect for family outings and romantic sunsets.
  2. Outdoor Adventures: Dive into vibrant underwater life with snorkeling gear and explore the natural beauty of the area.
  3. Rich Local Culture: Immerse yourself in the history and culture of Summerland Key through various excursions.
  4. Variety of Accommodations: Choose from spacious vacation homes, cozy cottages, and modern condos for your stay.
  5. Family-Friendly Activities: Engage in a range of activities that cater to both families and outdoor enthusiasts.

Popular types of accommodation in Summerland Key

Planning a getaway to Summerland Key? Exciting times await as you choose your perfect home away from home! Explore a range of popular vacation rentals, including charming cottages, spacious houses, and luxurious villa rentals. Don't miss the chance to stay at Sailfish Manor for a truly memorable experience. Dive into the options and find the ideal accommodation that suits your needs for a fantastic vacation!

  • Condos: The top choice for vacationers in Summerland Key, offering a blend of comfort and amenities.
  • Cottages: A charming option, cottages provide a cozy retreat amidst the scenic beauty of Summerland Key.
  • Houses: Ideal for families or groups, these homes offer privacy and ample space for relaxation.
  • House Boats: A unique experience, houseboats let you enjoy your vacation right on the water.
  • Apartments: A convenient choice for travelers seeking a home-like atmosphere during their stay.**

Top attractions in Summerland Key

Summerland Key offers a perfect blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Visitors can enjoy beautiful beaches, explore historic houses, and immerse themselves in local culture. For those seeking adventure, snorkeling gear is available to discover the vibrant underwater life. With a variety of attractions catering to beach lovers and outdoor enthusiasts, Summerland Key promises an unforgettable getaway for everyone.

  1. Florida Keys Beaches: A stunning beach located 8 miles from Summerland Key, offering pristine sands, crystal-clear waters, and a laid-back atmosphere perfect for sunbathing and swimming.
  2. Upper Sugarloaf Key: A charming neighborhood within Summerland Key, showcasing a vibrant community feel with local shops, dining options, and a welcoming ambiance that reflects the island lifestyle.
  3. Upper Sugarloaf Sound: A beautiful island featuring outdoor activities, ideal for kayaking, paddleboarding, and enjoying scenic beach vibes amidst nature's tranquility.

Things to do recommended for couples

For a romantic getaway in Summerland Key, consider a visit to Pigeon Key, located 18 miles away. Enjoy exhilarating water sports and embrace the outdoor adventure vibes together. It's the perfect blend of excitement and romance for couples looking to create lasting memories.

Things to do recommended for groups

Groups visiting Summerland Key can explore the vibrant Big Pine Key Flea Market for local treasures, enjoy a round of golf at the scenic Key West Golf Club, and immerse themselves in culture at the Tennessee Williams Fine Art Center, perfect for entertainment and family bonding.

What do I need to keep in mind when booking a vacation in Summerland Key

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Summerland Key with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your experience.
  • Taking your pets with you to Summerland Key: For many, a family vacation isn't truly fulfilling without their furry companions. If this resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Summerland Key: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Summerland Key

Summerland Key offers a tranquil island getaway perfect for outdoor enthusiasts and families alike. Explore pristine shores and enjoy the breathtaking sunsets at Sunset Beach, where the atmosphere is romantic and family-friendly. This hidden gem invites you to experience the beauty of nature while indulging in excursions that highlight the area's rich history. Discover the charm of Summerland Key and create unforgettable memories in this tropical paradise.

  • Key West: Key West, located 24 miles from Summerland Key, is a vibrant island city known for its lively atmosphere and rich history. Travelers flock here for a mix of family, city, and business experiences. Key West boasts an array of attractions, including beautiful beaches, bustling shopping areas, and charming streets filled with local art and culture. Don't miss the iconic Southernmost Point buoy, historic landmarks like Ernest Hemingway's home, and the breathtaking sunset celebrations at Mallory Square. With excellent dining options and a laid-back vibe, Key West is a must-visit destination for anyone exploring the Florida Keys.
  • Sugarloaf Shores: Nestled around Summerland Key, Sugarloaf Shores is a serene neighborhood perfect for outdoor and beach enthusiasts. This picturesque area offers a relaxed atmosphere with opportunities for family-friendly activities. Visitors can explore nearby beaches, indulge in recreational activities, and browse local shopping areas. The neighborhood is known for its stunning waterfront views and proximity to natural attractions, making it ideal for a day of sun and fun. Whether enjoying a beach picnic or taking a stroll along the shore, Sugarloaf Shores provides a peaceful escape in the Florida Keys.
  • Cutthroat Harbor Estates: Located near Summerland Key, Cutthroat Harbor Estates is a delightful neighborhood that caters to adventure seekers and beach lovers. The area offers plenty of outdoor activities, including water sports and recreational areas to explore. Visitors can enjoy beautiful beaches and stunning island views, as well as various shopping options. With its inviting atmosphere and focus on outdoor adventures, Cutthroat Harbor Estates is an excellent choice for those looking to immerse themselves in the natural beauty of the Florida Keys while enjoying exciting activities.

Best time to go to Summerland Key

If you're planning a trip to Summerland Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and July, while off-peak times, like May and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
May79.3°F (26.3°C)Light RainMostly SunnySlightly LowAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowAverage
November76.6°F (24.8°C)Light RainMostly SunnySlightly LowSlightly Low
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Flexibility with your travel dates can lead to significant savings, as prices can vary. Additionally, booking a longer stay often results in greater discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your total booking amount. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy and organized way to plan your trips, allowing you to start new adventures, continue from where you paused, or keep track of your travel plans. You can easily access your saved or booked properties, which are neatly categorized as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Book a vacation rental for your Summerland Key getaway

Learn about the unique charm of Summerland Key with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Where the cats have too many toes

Pick a key, any key. Summerland Key is a quiet, residential kinda place, so excursions might be on the menu. It's towards the western end of the Keys, meaning larger towns like Marathon and Key West are both around a half hour drive away. Macho literature aficionados will want to visit the Ernest Hemingway House in Key West, and see if they can count the toes on his resident mutant cats. While you're out that way, tour Harry S. Truman's Little White House, or take in some art at the Gallery on Greene and the Key West Historical Society.

The easiest Marathon you'll ever encounter

For such a laid-back place, a Summerland Key vacation rental gives you a lot of options. Fishermen can head over to the nearby sport-fishing capital of Marathon, or you could just stroll down to the water's edge and drop a line in. If you prefer to watch fish from a distance, then the snorkeling possibilities round here are immense. Try Looe Key marine sanctuary for something a bit special. Wildlife-watchers want to drive the 10 minutes to Big Pine Key, home to the dog-sized Key deer, or you could head a bit further out to the Dolphin Research Center.

Well they don't call it "Winterland," do they?

How does that saying go? Wherever you are in the world, the weather is probably better in the Keys. A Summerland Key vacation rental dishes up weather that you can only describe as tropical. The winter runs between November and May, though all "winter" means in the Florida Keys is that it doesn't rain as much. Otherwise it's still going to be balmy. You won't see a flake of snow, and in fact the temperature hasn't dropped below freezing since records began. As for summer, it'll be hot, and it'll pour with rain each afternoon. Bring a raincoat.

There's a reason those Key deer never leave

The Florida Keys are an archipelago off the coast of Florida, between the Gulf of Mexico and the Atlantic Ocean. They're actually the above-water bits of a massive coral reef that started forming more than a 100,000 years ago. Because the climate's so mild, all kinds of stuff thrives here that doesn't exist further north. Hell, some of it doesn't even exist outside the Keys, like Key deer and the Key Largo woodrat. And then there are the creatures that live in the water. Marine life is bountiful, but the crocodiles and the dolphins are the real celebrities.

Transportation options to and around Summerland Key

The nearest airport is in Key West Intl. Airport (EYW), located 20.9 mi (33.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 25.1 mi (40.3 km) away.

Frequently asked questions

What is the best area to stay in Summerland Key when booking a vacation rental?
When considering a vacation rental in Summerland Key, a popular area to stay is the Summerland Key Isles neighborhood. This picturesque community features a variety of waterfront properties, making it ideal for those who enjoy boating or fishing. With a good number of vacation rentals available, you can find charming homes that offer direct access to the water.

One of the top attractions nearby is the beautiful Looe Key National Marine Sanctuary, renowned for its stunning coral reefs and abundant marine life. This makes it a great spot for snorkeling and diving enthusiasts. Additionally, the relaxed atmosphere of the area allows you to unwind and enjoy the natural beauty of the Florida Keys.

Another appealing location within Summerland Key is the area around the iconic Summerland Key Park. This tranquil spot is great for leisurely walks, picnicking, and simply soaking in the views.
How much does it cost to rent a vacation home in Summerland Key?
Prices for vacation rentals in Summerland Key vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Summerland Key to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Summerland Key vacation house rentals?
You can find great discounts on house rentals in Summerland Key on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Summerland Key?
For renting a beach house in Summerland Key, Florida, travelers should explore the picturesque waterfront neighborhoods that offer direct access to the stunning Florida Keys waters. The area around the Summerland Key Canal is particularly appealing, where vacation rentals often come equipped with private boat docks, allowing for easy boating and fishing excursions. Many properties in this vicinity feature spacious outdoor decks, pools, and lush tropical landscaping, great for enjoying the warm climate and beautiful sunsets.

Another great option is the vicinity of the nearby Bahia Honda State Park, known for its pristine beaches and clear waters. Rentals here may offer amenities such as kayaks or paddleboards, providing guests with the opportunity to explore the natural beauty of the area. Properties in this area often have open-concept living spaces, modern kitchens, and large windows that bring in plenty of natural light, enhancing the vacation experience.

Additionally, the local area is rich in activities, with nearby attractions like the Looe Key Reef for snorkeling and diving, as well as various restaurants and shops that reflect the laid-back island lifestyle. Find your rental near the beach in Summerland Key.
What is the most popular type of vacation rental accomodation in Summerland Key?
In Summerland Key, vacation houses are the most popular type of accommodation, with approximately 457 options available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor patios or decks, ideal for enjoying the stunning waterfront views and the tropical climate. Many of these properties are located near the beach and offer easy access to local points of interest such as Looe Key National Marine Sanctuary and John Pennekamp Coral Reef State Park.

In addition to vacation houses, there are around 50 cottages that provide a charming, cozy atmosphere, often with quaint decor and essential amenities for a comfortable stay. For those seeking a great experience, about 28 campsites are available in the vicinity, allowing travelers to immerse themselves in nature. Mobile homes, although fewer in number at 19, also provide a budget-friendly option for visitors.
Are there any family house rentals in Summerland Key?
In Summerland Key, Florida, families will find an impressive selection of vacation rentals, with around 333 properties suiting group needs. This area is known for its stunning waterfront views and easy access to outdoor activities, making it an ideal spot for family getaways. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play or for family barbecues.

Visitors can enjoy amenities such as private pools, game rooms, and direct access to the water for fishing or kayaking, enhancing the overall experience. Nearby attractions include beautiful beaches and natural parks, which provide opportunities for hiking and exploring the unique Florida Keys ecosystem. See all family-friendly rentals in Summerland Key.
Can I rent a vacation home with a pool or hot tub in Summerland Key?
In Summerland Key, there are plenty of vacation homes available for rent that come equipped with pools and hot tubs, with around 363 options to choose from. This picturesque island community in the Florida Keys offers an inviting tropical atmosphere, superb for relaxation and recreation. Travelers can expect many amenities in these rentals, including private swimming pools, outdoor hot tubs, and spacious decks ideal for soaking up the sun. Many properties also feature fully equipped kitchens, providing the convenience of preparing meals after a day of exploration.

The area is known for its stunning waterfront views and easy access to activities such as boating, fishing, and snorkeling. Find your rental in Summerland Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Summerland Key?
A long-stay vacation rental in Summerland Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Summerland Key?
In Summerland Key, there are numerous pet-friendly house rentals available, with around 272 options to choose from. This beautiful community in the Florida Keys offers a range of vacation homes that often come with amenities such as private pools, outdoor patios, and fully equipped kitchens, making them great for families and groups traveling with pets.

Many of these rentals are situated close to the water, providing easy access to waterfront activities, and some properties even feature docks for boating enthusiasts. The serene environment and tropical landscapes enhance the experience, allowing guests to enjoy the outdoors with their furry companions.

Furthermore, nearby attractions like the National Key Deer Refuge offer scenic walking trails where pets are welcome, making it a great area for outdoor adventures. See all pet-friendly rentals in Summerland Key.
Are there any remote work vacation rentals in Summerland Key?
In Summerland Key, there are numerous vacation rentals that cater to remote work needs, with around 453 options available. This picturesque island destination offers a blend of tropical charm and modern amenities, making it great for those looking to work while enjoying a serene environment. Many properties come equipped with dedicated workspaces, including desks and ergonomic chairs, along with high-speed Wi-Fi to ensure reliable connectivity.

Travelers can expect amenities such as fully equipped kitchens, outdoor patios, and private pools, providing a comfortable and productive atmosphere. The area is known for its stunning waterfront views, making it easy to unwind after a day of work. Additionally, the proximity to local attractions like the nearby beaches and nature parks allows for a refreshing break during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Summerland Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Summerland Key with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Summerland Key?
In Summerland Key, popular vacation rental amenities include WiFi, kitchens, and pools, making them ideal for travelers seeking comfort and convenience. Many rentals come equipped with a blender and a coffee/tea maker, allowing guests to prepare meals and enjoy coffee in the comfort of their accommodations.
When is the best time to visit Summerland Key for a vacation rental?
The best time to visit Summerland Key for a vacation rental is during the summer months, particularly in July. This is when the area truly comes alive, attracting sun-seekers and water enthusiasts eager to enjoy the warm, tropical climate. With temperatures typically hovering in the mid-80s to low 90s Fahrenheit, July provides great conditions for swimming, snorkeling, and exploring the vibrant marine life that the Florida Keys are famous for.

As you plan your adventure, keep in mind that the peak tourist season extends from July to September. This period offers a wealth of outdoor activities, including kayaking through the serene mangroves and soaking up the sun on pristine beaches. The lively atmosphere is enhanced by local events and festivities, making it an ideal time for those looking to connect with fellow travelers and experience the local culture.

For those seeking a more budget-conscious option, consider visiting in October. This month presents a wonderful opportunity to enjoy the area's natural beauty without the crowds, as the weather remains pleasant, with temperatures typically in the low 80s Fahrenheit. You can still partake in outdoor activities like fishing and hiking, all while benefiting from lower rental rates.

Ultimately, whether you choose the vibrant summer season or the quieter fall months, Summerland Key promises unforgettable experiences tailored to your preferences.
How early should I book a Summerland Key vacation rental?
Book your Summerland Key vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Summerland Key?
In Summerland Key, visitors can enjoy a range of attractions within this beautiful island community. The area is known for its stunning waterfront views and access to various water activities, making it a prime spot for fishing, snorkeling, and kayaking. Vacation rentals near the Summerland Key Marina offer convenient access to boat rentals and fishing charters.

For those interested in nature, the nearby Florida Keys National Marine Sanctuary provides opportunities for eco-tourism and exploration of the vibrant marine life. The relaxed atmosphere of Summerland Key is complemented by local dining options, where visitors can savor fresh seafood and enjoy the laid-back island vibe. Additionally, the nearby Bahia Honda State Park offers beautiful beaches and hiking trails, appealing to outdoor enthusiasts.
Can I change or cancel my Summerland Key home rental booking on Vrbo?
To find Summerland Key vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

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